KEGG   PATHWAY: rn00902
Entry
rn00902                     Pathway                                
Name
Monoterpenoid biosynthesis
Description
Monoterpenoids (C10 terpenoids) are a group of terpenoids consisting of two isoprene units. They are derived from geranyl diphosphate (GPP). Most monoterpenoids are volatile oils with highly distinctive aromas and flavors, such as essential oils, turpentine, and oleoresins of coniferous plants. This map shows some examples. The monoterpene ketone l-menthone is specifically converted to l-menthol and d-neomenthol in mature peppermint leaves. The iridoids constitute a family of highly oxygenated monoterpenes, mixtures of which are present in many medicinal plants, such as valerian. They are derived from geraniol or nerol via oxidation of a terminal methyl group. The cyclopentane ring of loganin can itself be cleaved in a further P450-dependent step, leading to secologanin, which provides the carbon skeleton for many powerfully bioactive secondary metabolites of indole alkaloids.
Class
Metabolism; Metabolism of terpenoids and polyketides
Pathway map
rn00902  Monoterpenoid biosynthesis
rn00902

Other DBs
GO: 0016099
Reaction
R02004  geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-endo-fenchol-forming]
R02006  geranyl-diphosphate diphosphate-lyase (cyclizing, sabinene-hydrate-forming)
R02007  (+)-bornyl-diphosphate lyase (decyclizing)
R02009  geranyldiphosphate diphosphate-lyase (myrcene-forming)
R02013  geranyl-diphosphate diphosphate-lyase [cyclizing; (4S)-limonene-forming]
R02177  (-)-menthol:NADP+ oxidoreductase
R02468  (S)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
R02469  (S)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
R02470  (S)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7-hydroxylating)
R02548  (+)-neomenthol:NADP+ oxidoreductase
R02944  (+)-borneol:NAD+ oxidoreductase
R02994  6-endo-hydroxycineole:NAD+ 6-oxidoreductase
R02995  6-oxocineole,NADPH:oxygen oxidoreductase
R03114  (-)-trans-carveol:NADP+ oxidoreductase
R03261  (-)-trans-isopiperitenol:NAD+ oxidoreductase
R03554  S-adenosyl-L-methionine:loganate 11-O-methyltransferase
R03555  loganin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (ring-cleaving)
R03556  7-deoxyloganin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7alpha-hydroxylating)
R04578  
R05090  
R05765  geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-alpha-pinene-forming]
R05766  geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-beta-pinene-forming]
R05832  7-deoxyloganate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7alpha-hydroxylating)
R05833  loganate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (ring-cleaving)
R05834  S-adenosyl-L-methionine:secologanate 11-O-methyltransferase
R05898  
R05899  
R05900  
R06117  (+)-trans-carveol: NAD+ oxidoreductase
R06119  (R)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
R06120  geranyldiphosphate diphosphate lyase [(+)-(R)-limonene-forming]
R06417  (+)-cis-isopulegone:NADP+ oxidoreductase
R06418  (+)-cis-isopulegone isomerase
R06419  (-)-menthone:NADP+ oxidoreductase
R06420  (+)-pulegone reductase
R06421  geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-alpha-terpineol-forming]
R06422  
R07631  geranyl-diphosphate diphosphate-lyase [(3S)-linalool-forming]
R07632  geranyl-diphosphate diphosphate-lyase [(3R)-linalool-forming]
R08396  geranyl-diphosphate diphosphohydrolase
R08499  (6E)-8-hydroxygeraniol:NADP+ oxidoreductase
R08500  
R08529  monoterpenyl-diphosphate pyrophosphohydrolase
R08784  1,8-cineole,[reduced flavodoxin]:oxygen oxidoreductase (2-endo-hydroxylating)
R08785  geraniol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
R08923  (+)-pulegone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (9-hydroxylating)
R08925  (-)-menthone,NADPH:oxygen oxidoreductase
R09702  (+)-linalool hydro-lyase (myrcene-forming)
R09708  geraniol hydroxymutase
R09922  (+)-linalool,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
R09923  (-)-linalool,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
R09924  8-hydroxylinalool,[reduced NADPH---hemoprotein reductase]:oxygen 8-oxidoreductase
R09963  geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming]
R09971  geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-camphene-forming]
R09972  geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-camphene-forming]
R10834  UDP-alpha-D-glucose:7-deoxyloganetate O-D-glucosyltransferase
R10835  UDP-alpha-D-glucose:7-deoxyloganetin O-D-glucosyltransferase
R10918  (R)-ipsdienol:NAD+ oxidoreductase
R10919  (R)-ipsdienol:NADP+ oxidoreductase
R11055  myrcene,NADPH---hemoprotein reductase:O2 oxidoreductase (hydroxylating)
R11551  geranyl-diphosphate phosphohydrolase
R11552  geranyl-phosphate phosphohydrolase
R12182  iridotrial,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R12231  (+)-cis,trans-nepetalactol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R12253  7-deoxyloganetic alcohol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R12517  (S)-8-oxocitronellyl enol:NAD+ oxidoreductase
R12518  (S)-8-oxocitronellyl enol:NADP+ oxidoreductase
R12520  (S)-8-oxocitronellyl enol cyclase [(+)-cis,trans-nepetalactol-forming]
Compound
C00341  Geranyl diphosphate
C00400  (-)-Menthol
C00521  (S)-Limonene
C00553  (+)-Neomenthol
C00808  (+)-Camphor
C00843  (-)-Menthone
C00848  6-Oxocineole
C00964  (-)-trans-Carveol
C01123  (-)-trans-Isopiperitenol
C01433  Loganin
C01500  Geraniol
C01512  Loganate
C01765  (+)-Borneol
C01767  (-)-Carvone
C01852  Secologanin
C01957  Secologanate
C02344  (-)-endo-Fenchol
C02452  (-)-Perillyl alcohol
C02462  Sabinene hydrate
C02485  (-)-Isopiperitenone
C03092  6-endo-Hydroxycineole
C03190  (+)-Bornyl diphosphate
C04433  (6E)-8-Hydroxylinalool
C04718  1,6,6-Trimethyl-2,7-dioxabicyclo[3.2.2]nonan-3-one
C06066  4,5-Dihydro-5,5-dimethyl-4-(3-oxobutyl)furan-2(3H)-one
C06070  Iridotrial
C06071  Deoxyloganin
C06074  Myrcene
C06099  (R)-Limonene
C06304  (+)-Camphene
C06305  (-)-Camphene
C06307  (-)-beta-Pinene
C06308  (-)-alpha-Pinene
C09769  Asperuloside
C09782  Gentiopicrin
C09804  cis-trans-Nepetalactol
C09844  1,8-Cineole
C09893  Pulegone
C11382  (+)-3-Carene
C11383  (+)-(S)-Carvone
C11388  (-)-Linalool
C11389  (+)-Linalool
C11393  (-)-alpha-Terpineol
C11409  (+)-trans-Carveol
C11636  7-Deoxyloganate
C11672  10-Deoxygeniposidic acid
C11673  Geniposidic acid
C11951  (+)-cis-Isopulegone
C11952  (+)-Isomenthone
C17621  (6E)-8-Hydroxygeraniol
C17622  (6E)-8-Oxogeranial
C18025  (+)-Menthofuran
C18027  (4R,7S)-7-Isopropyl-4-methyloxepan-2-one
C20221  (6E)-8-Oxolinalool
C20789  7-Deoxyloganetate
C20790  7-Deoxyloganetin
C20943  (R)-Ipsdienol
C20944  Ipsdienone
C21203  Geranyl phosphate
C22014  7-Deoxyloganetic alcohol
C22225  (S)-8-Oxocitronellyl enol
Reference
PMID:15728344
  Authors
Davis EM, Ringer KL, McConkey ME, Croteau R
  Title
Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint.
  Journal
Plant Physiol 137:873-81 (2005)
DOI:10.1104/pp.104.053306
Reference
PMID:11375201
  Authors
Duetz WA, Fjallman AH, Ren S, Jourdat C, Witholt B
  Title
Biotransformation of D-limonene to (+) trans-carveol by toluene-grown Rhodococcus opacus PWD4 cells.
  Journal
Appl Environ Microbiol 67:2829-32 (2001)
DOI:10.1128/AEM.67.6.2829-2832.2001
Reference
PMID:15299125
  Authors
Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D
  Title
Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole.
  Journal
Plant Physiol 135:1956-66 (2004)
DOI:10.1104/pp.104.044388
Reference
PMID:1368150
  Authors
Trudgill PW
  Title
Microbial metabolism of monoterpenes--recent developments.
  Journal
Biodegradation 1:93-105 (1990)
DOI:10.1007/BF00058829
Reference
PMID:1864846
  Authors
Ikeda H, Esaki N, Nakai S, Hashimoto K, Uesato S, Soda K, Fujita T
  Title
Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols.
  Journal
J Biochem 109:341-7 (1991)
Reference
PMID:10656401
  Authors
Yamamoto H, Katano N, Ooi A, Inoue K.
  Title
Secologanin synthase which catalyzes the oxidative cleavage of loganin into secologanin is a cytochrome P450.
  Journal
Phytochemistry 53:7-12 (2000)
DOI:10.1016/S0031-9422(99)00471-9
Reference
PMID:11524113
  Authors
Katano N, Yamamoto H, Iio R, Inoue K.
  Title
7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures.
  Journal
Phytochemistry 58:53-8 (2001)
DOI:10.1016/S0031-9422(01)00181-9
Related
pathway
rn00900  Terpenoid backbone biosynthesis
rn00901  Indole alkaloid biosynthesis
rn00903  Limonene degradation
rn00907  Pinene, camphor and geraniol degradation
KO pathway
ko00902   

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